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Issue 22, 2018
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Nickel catalyzed regio- and stereoselective arylation and methylation of allenamides via coupling reactions. An experimental and computational study

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Abstract

The nickel catalyzed regio- and stereoselective condensation of boronic acids to allenamides is documented as a novel synthetic route to stereochemically defined tri-substituted enamides. The protocol has been implemented into a three-component variant intercepting the in situ formed allyl-Ni intermediate with a range of aldehydes. Additionally, evidence for the effective extension of this methodology to Me2Zn is documented. Full rationale on the mechanism as well as its stereochemical outcome is provided by a synergistic experimental/computational approach.

Graphical abstract: Nickel catalyzed regio- and stereoselective arylation and methylation of allenamides via coupling reactions. An experimental and computational study

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Publication details

The article was received on 17 Jul 2018, accepted on 29 Sep 2018 and first published on 29 Sep 2018


Article type: Research Article
DOI: 10.1039/C8QO00729B
Citation: Org. Chem. Front., 2018,5, 3231-3239
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    Nickel catalyzed regio- and stereoselective arylation and methylation of allenamides via coupling reactions. An experimental and computational study

    Y. Liu, A. Cerveri, A. De Nisi, M. Monari, O. Nieto Faza, C. S. Lopez and M. Bandini, Org. Chem. Front., 2018, 5, 3231
    DOI: 10.1039/C8QO00729B

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